(4-fluoropiperidin-4-yl)methanol;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of tert-butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (21 g, 0.09 mol) in dry ether (200 mL) was added HCl/ether (4M, 100 mL) drop-wise at 0° C. under N2. After addition, the mixture was allowed to warm to RT and stirred overnight. The reaction mixture was concentrated to remove solvent and the residue was washed with ether. 1H NMR (400 MHz, D2O): δ 1.78 (m, 2H), 2.05 (m, 2H), 3.15 (m, 2H), 3.31 (m, 2H), 3.57 (d, 2H), m/z 134 [M+H]+. After addition The reaction mixture was concentrated to remove solvent the residue was washed with ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of tert-butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (21 g, 0.09 mol) in dry ether (200 mL) was added HCl/ether (4M, 100 mL) drop-wise at 0° C. under N2. After addition, the mixture was allowed to warm to RT and stirred overnight. The reaction mixture was concentrated to remove solvent and the residue was washed with ether. 1H NMR (400 MHz, D2O): δ 1.78 (m, 2H), 2.05 (m, 2H), 3.15 (m, 2H), 3.31 (m, 2H), 3.57 (d, 2H), m/z 134 [M+H]+. After addition The reaction mixture was concentrated to remove solvent the residue was washed with ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 4 N solution of hydrochloric acid in 1,4-dioxane (213 μL) was added to a solution of 4-fluoro-4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (24.9 mg, 0.107 μmol) in MeOH (213 μL) at room temperature, and the mixture was stirred at room temperature for two hours. The reaction solution was concentrated under reduced pressure to give (4-fluoro-piperidin-4-yl)-methanol hydrochloride as a brown form (19.6 mg). The reaction solution was concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of tert-butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (21 g, 0.09 mol) in dry ether (200 mL) was added HCl/ether (4M, 100 mL) drop-wise at 0° C. under N2. After addition, the mixture was allowed to warm to RT and stirred overnight. The reaction mixture was concentrated to remove solvent and the residue was washed with ether. 1H NMR (400 MHz, D2O): δ 1.78 (m, 2H), 2.05 (m, 2H), 3.15 (m, 2H), 3.31 (m, 2H), 3.57 (d, 2H), m/z 134 [M+H]+. After addition The reaction mixture was concentrated to remove solvent the residue was washed with ether